4-(4-Nitrobenzylideneamine)phenol was used in two strategies allowing the highly selective detection of F- and CN-. Firstly, the compound in acetonitrile acts as a chromogenic chemosensor based on the idea that more basic anions cause its deprotonation (colorless solution), generating a colored solution containing phenolate. The discrimination of CN- over F- was obtained by adding 1.4% water to acetonitrile: water preferentially solvates F-, leaving the CN- free to deprotonate the compound. Another strategy involved an assay comprised of the competition between phenolate dye and the analyte for calix[4]pyrrole in acetonitrile, a receptor highly selective for F-. Phenolate and calix[4]pyrrole form a hydrogen-bonded complex, which changes the color of the medium. On the addition of various anions, only F- was able to restore the original color corresponding to phenolate in solution due to the fact that the anion dislodges phenolate from the complexation site.